JP5164510B2 - Nitrogen-containing heterocyclic compounds and pest control agents - Google Patents

Description

  The present invention relates to a novel nitrogen-containing heterocyclic compound, a salt of this compound, and a pest control agent containing these compounds as active ingredients.

  Conventionally, many pesticides such as insecticides and acaricides have been used, but their efficacy is insufficient, their use is limited due to drug resistance problems, and phytotoxicity to plants. In many cases, it is not always a satisfactory control drug because it causes pollution and pollution, or is highly toxic to livestock fish. Therefore, there is a demand for the development of a drug that can be safely used with few such drawbacks.

In relation to the present invention, Patent Document 1 describes the following isoxazoline-substituted compound having a skeleton similar to that of the compound of the present invention.
However, this document does not describe the compound of the present invention.

Wherein W ′ represents an oxygen atom or a sulfur atom, A ^a , A ^b and ^Ac each independently represent a carbon atom or a nitrogen atom, Y ′ represents a halogen atom or the like, and n ′ is 0 Or R ¹ , R ^b each independently represents a hydrogen atom, a C1-12 alkyl group or the like, R ^c represents a halogen atom or the like, and G ′ represents a phenyl group or the like.)
WO2005 / 085216 pamphlet

  The present invention provides a novel nitrogen-containing heterocyclic compound that can be synthesized industrially advantageously, can be used safely as an active ingredient of a pest control agent that can be used safely and safely, and a pest control agent containing this compound as an active ingredient. The issue is to provide.

  In order to solve the above problems, the present invention firstly provides a compound of formula (I)

[Wherein W represents an oxygen atom or a sulfur atom.
A ₁ , A ₂ and A ₃ each independently represent a carbon atom or a nitrogen atom.
X represents a carbon atom or an oxygen atom.
Y represents a halogen atom, cyano group, nitro group, formyl group, C1-C6 alkyl group, C2-C6 alkenyl group, C2-C6 alkynyl group, C1-C6 haloalkyl group, C3-C8 cycloalkyl group, C3-C8 halo group. A cycloalkyl group, a hydroxyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C1-C6 alkylsulfonyloxy group, an unsubstituted or substituted phenylsulfonyloxy group, a mercapto group, a C1-C6 alkylthio group, a C1- C6 alkylsulfenyl group, C1-C6 alkylsulfonyl group, C1-C6 haloalkylthio group, C1-C6 haloalkylsulfenyl group, C1-C6 haloalkylsulfonyl group, unsubstituted or substituted phenylthio group, unsubstituted or substituted Phenylsulfenyl group having Unsubstituted or phenylsulfonyl group having a substituent, an amino group, a mono C1~C6 alkylamino group, di-C1~C6 alkyl amino group, an acylamino group, a phenyl group which carries an unsubstituted or substituted group, -N = C (R ₃₎ a group represented by OR _4, groups represented by _{-CO 2 R 3, -C (=} O) N (R 3) ( the groups represented by _{R 4), -C (= S} ) N ( A group represented by R ₃ ) (R ₄ ), a group represented by —Si (R ₅ ) (R ₆ ) (R ₇ ), an unsubstituted or substituted phenyl group, or an unsubstituted or substituted group; Represents a heterocyclic group having

R ₃ and R ₄ are each independently a hydrogen atom, a C1-C12 alkyl group, a C1-C12 haloalkyl group, a C3-C12 cycloalkyl group, a C2-C12 alkenyl group, a C2-C12 haloalkenyl group, a C2-C12 alkynyl group. Group, C2-C12 haloalkynyl group, C1-C12 alkylthio group, hydroxyl group, C1-C12 alkoxy group, amino group, mono C1-C6 alkylamino group, di-C1-C6 alkylamino group, acylamino group, unsubstituted or substituted Represents a phenylamino group having a substituent, a phenyl group having an unsubstituted or substituted group, or a heterocyclic group having an unsubstituted or substituted group.

R _{5 to} R ₇ each independently represents a hydrogen atom, a C 1 to C 12 alkyl group, or an unsubstituted or substituted phenyl group.
n represents an integer of 0 to 4. When n is 2 or more, the plurality of Y may be the same as or different from each other.
When two Ys are adjacent to each other, the two Ys may be bonded together to form a 5-membered ring or a 6-membered ring.

Q is a hydrogen atom, halogen atom, cyano group, formyl group, oxo group, C1-C12 alkyl group, C2-C6 alkenyl group, C2-C6 alkynyl group, C1-C12 haloalkyl group, C3-C8 cycloalkyl group, C3 -C8 halocycloalkyl group, hydroxyl group, C1-C6 alkoxy group, C1-C6 haloalkoxy group, C1-C6 alkylsulfonyloxy group, unsubstituted or substituted phenylsulfonyloxy group, mercapto group, C1-C6 alkylthio group , C1-C6 alkylsulfenyl group, C1-C6 alkylsulfonyl group, C1-C6 haloalkylthio group, C1-C6 haloalkylsulfenyl group, C1-C6 haloalkylsulfonyl group, unsubstituted or substituted phenylthio group, unsubstituted Or substituted phenyl Ruphenyl group, unsubstituted or substituted phenylsulfonyl group, amino group, mono C1-C6 alkylamino group, di-C1-C6 alkylamino group, acylamino group, unsubstituted or substituted phenylamino group, -C ( = O) R ₈ group, -CO ₂ R ₈ group, -OC (= O) R ₈ group, -C (= O) SR ₈ group, -C (= S) group represented by OR _8, -C (= S) groups represented by _{SR 8, -C (= S)} N (R 8) a group represented by _{(R 9),} - A group represented by N = C (R ₈ ) OR ₉ , a group represented by —C (═O) N (R ₈ ) (R ₉ ), —C (═S) N (R ₈ ) (R _{9 ),} a group represented by the group represented by _{-Si (R 10) (R 11} ) (R 12), phenyl group having unsubstituted or substituted, or Mu置Or a heterocyclic group having a substituent.

R ₈ and R ₉ are each independently a hydrogen atom, C1-C12 alkyl group, C1-C12 haloalkyl group, C3-C12 cycloalkyl group, C2-C12 alkenyl group, C2-C12 haloalkenyl group, C2-C12 alkynyl. Group, C2-C12 haloalkynyl group, C1-C12 alkylthio group, hydroxyl group, C1-C12 alkoxy group, amino group, mono C1-C6 alkylamino group, di-C1-C6 alkylamino group, acylamino group, unsubstituted or substituted Represents a phenylamino group having a substituent, a phenyl group having an unsubstituted or substituted group, or a heterocyclic group having an unsubstituted or substituted group.

R _{10 to} R ₁₂ each independently represents a hydrogen atom, a C1-C12 alkyl group, a C1-C12 haloalkyl group, or an unsubstituted or substituted phenyl group.
q represents an integer of 0 to 7.
When q is 2 or more, the plurality of Q may be the same as or different from each other.
Z represents an unsubstituted or substituted phenyl group, or an unsubstituted or substituted heterocyclic group.

R ₁ and R ₂ are each independently a hydrogen atom, a cyano group, a C1-C12 alkyl group optionally substituted by G, a C3-C12 cycloalkyl group optionally substituted by G, or a G-substituted group. An optionally substituted C2-C12 alkenyl group, a C3-C12 cycloalkenyl group optionally substituted by G, a C2-C12 alkynyl group optionally substituted by G, a mercapto group, a C1-C6 alkylthio group, a C1- A C6 alkylsulfonyl group, an unsubstituted or substituted phenylthio group, an unsubstituted or substituted phenylsulfonyl group, a group represented by —SN (R ₁₃ ) (R ₁₄ ), —S (O) ₂ N ( R _{13) (the} groups represented by _{R 14),} hydroxyl group, an amino group, a group represented by _{-OR 13, -N (R 13)} (R 14 A group represented by a group represented by _{-N = CH (R 13),} -N = C (R 13) groups represented by _{(R 14),} represented by -C (= _{O) R 13 group,} a group represented by _{-CO 2 R 13, -C (=} O) groups represented by _{SR 13, -C (= O)} N (R 13) groups represented by _{(R 14),} -C A group represented by (= S) OR ₁₃ , a group represented by -C (= S) SR ₁₃ , a group represented by -C (= S) N (R ₁₃ ) (R ₁₄ ), -C ( = NR ₁₃ ) OR ₁₄ group, -C (= NR ₁₃ ) SR ₁₄ group, -C (= NR ₁₃ ) N (R ₁₄ ) (R ₁₅ ) group, A substituted or substituted phenyl group or an unsubstituted or substituted heterocyclic group is represented.

R ₁ and R ₂ may be bonded together to form a group represented by ═C (R ₁₃ ) (R ₁₄ ), and R ₁ and R ₂ are combined together. It may combine to form a 3- to 8-membered ring.

R _{13 to} R ₁₅ are each independently a hydrogen atom, a C1-C12 alkyl group, a C1-C12 haloalkyl group, a C3-C12 cycloalkyl group, a C2-C12 alkenyl group, a C2-C12 haloalkenyl group, a C2-C12. Alkynyl group, C2-C12 haloalkynyl group, C1-C12 alkylthio group, hydroxyl group, C1-C12 alkoxy group, amino group, mono C1-C6 alkylamino group, di-C1-C6 alkylamino group, acylamino group, unsubstituted or substituted It represents a phenylamino group having a group, an unsubstituted or substituted phenyl group, or an unsubstituted or substituted heterocyclic group.

G is a halogen atom, a cyano group, a C3-C8 cycloalkyl group, a C3-C8 halocycloalkyl group, a hydroxyl group, a C1-C6 alkylsulfonyloxy group, an unsubstituted or substituted phenylsulfonyloxy group, a mercapto group, C1 -C6 alkylthio group, C1-C6 alkylsulfenyl group, C1-C6 alkylsulfonyl group, C1-C6 haloalkylthio group, C1-C6 haloalkylsulfenyl group, C1-C6 haloalkylsulfonyl group, unsubstituted or substituted phenylthio group, sulphenyl group having unsubstituted or substituted, represented by a phenylsulfonyl group having unsubstituted or substituted group, an amino group, a group represented by _{-OR 16, -N (R 16)} (R 17) A group represented by —N═CH (R ₁₆ ), —N═C A group represented by (R ₁₆ ) (R ₁₇ ), a group represented by —C (═O) R ₁₆ , a group represented by —CO ₂ R ₁₆ , and a group represented by —C (═O) SR _16. A group represented by -C (= O) N (R ₁₆ ) (R ₁₇ ), a group represented by -C (= S) OR ₁₆ , and a group represented by -C (= S) SR ₁₆ Group, a group represented by —C (═S) N (R ₁₆ ) (R ₁₇ ), a group represented by —C (═NR ₁₆ ) OR ₁₇ , and a group represented by —C (= NR ₁₆ ) SR ₁₇ A group represented by —C (═NR ₁₆ ) N (R ₁₇ ) (R ₁₈ ), a group represented by —Si (R ₁₉ ) (R ₂₀ ) (R ₂₁ ), unsubstituted or substituted Or a heterocyclic group having no substituent or a substituent.

R _{16 to} R ₁₈ are each independently a hydrogen atom, a C1-C12 alkyl group, a C1-C12 haloalkyl group, a C3-C12 cycloalkyl group, a C2-C12 alkenyl group, a C2-C12 haloalkenyl group, a C2-C12 alkynyl. Group, C2-C12 haloalkynyl group, C1-C12 alkylthio group, hydroxyl group, C1-C12 alkoxy group, amino group, mono C1-C6 alkylamino group, di-C1-C6 alkylamino group, acylamino group, unsubstituted or substituted Represents a phenylamino group having a substituent, a phenyl group having an unsubstituted or substituted group, or a heterocyclic group having an unsubstituted or substituted group.

R _{19 to} R ₂₁ each independently represent a hydrogen atom, a C1-C12 alkyl group, a C1-C12 haloalkyl group, or an unsubstituted or substituted phenyl group.
s represents 0 or 1. ]
The nitrogen-containing heterocyclic compound represented by these, or its salt is provided.

Secondly, the present invention provides a pest control agent containing as an active ingredient at least one of the nitrogen-containing heterocyclic compound of the present invention or a salt thereof.
The pest control agent of the present invention is preferably an insecticide or an acaricide.

  According to the present invention, a novel nitrogen-containing heterocyclic compound or a salt thereof which can be synthesized industrially advantageously, can be used as an active ingredient of a pest control agent which can be used safely and safely, and at least one of these compounds are effective. A pest control agent as a component is provided.

Hereinafter, the present invention will be described in detail.
1) Nitrogen-containing heterocyclic compound represented by formula (I) or salt thereof The first of the present invention is a nitrogen-containing heterocyclic compound represented by formula (I) or a salt thereof.
In formula (1), W represents an oxygen atom or a sulfur atom.
A ₁ , A ₂ and A ₃ each independently represent a carbon atom or a nitrogen atom.
The following formula (A)

Specific examples of the partial structure represented by the following include the following.

Y represents a halogen atom such as a fluorine atom, a chlorine atom or a bromine atom; a cyano group; a nitro group; a formyl group; a C1-C6 alkyl group such as a methyl group, an ethyl group, an n-propyl group or an isopropyl group; a vinyl group or a propenyl group Groups, C2-C6 alkenyl groups such as isopropenyl group and 2-butenyl group; C2-C6 alkynyl groups such as propargyl group and 3-butynyl group; C1-C6 haloalkyl groups such as trifluoromethyl group and pentafluoroethyl group; C3-C8 cycloalkyl group such as cyclopropyl group, cyclopentyl group, cyclohexyl group; C3-C8 such as 2-chlorocyclopropyl group, 2,2-dichlorocyclopropyl group, 3-chlorocyclopentyl group, 4-bromocyclohexyl group, etc. Halocycloalkyl group; hydroxyl group; methoxy group, ethoxy group, n-propoxy group, C1-C6 alkoxy groups such as propoxy group, n-butoxy group, t-butoxy group; C1-C6 haloalkoxy groups such as trichloromethoxy group, trifluoromethoxy group; methylsulfonyloxy group, ethylsulfonyloxy group, n-propyl C1-C6 alkylsulfonyloxy group such as sulfonyloxy group; phenylsulfonyloxy group having unsubstituted or substituted such as phenylsulfonyloxy group, 4-methylphenylsulfonyloxy group; mercapto group; methylthio group, ethylthio group, n- C1-C6 alkylthio groups such as propylthio group, isopropylthio group, n-butylthio group, t-butylthio group; C1-C6 alkylsulfenyl groups such as methylsulfenyl group, ethylsulfenyl group, propylsulfenyl group; Base C1-C6 alkylsulfonyl groups such as ethylsulfonyl group and n-propylsulfonyl group; C1-C6 haloalkylthio groups such as chloromethylthio group, trichloromethylthio group and trifluoromethylthio group; chloromethylsulfenyl group, trichloromethylsulfenyl group, C1-C6 haloalkylsulfenyl group such as trifluoromethylsulfenyl group; C1-C6 haloalkylsulfonyl group such as chloromethylsulfonyl group, trichloromethylsulfonyl group, trifluoromethylsulfonyl group; phenylthio group, 4-methylphenylthio group, Unsubstituted or substituted phenylthio group such as 2,4-dichlorophenylthio group; Unsubstituted such as phenylsulfenyl group, 4-methylphenylsulfenyl group, 2,4-dichlorophenylsulfenyl group Or phenylsulfenyl group having a substituent; phenylsulfonyl group having an unsubstituted or substituted group such as phenylsulfonyl group, 4-methylphenylsulfonyl group, 2,4-dichlorophenylsulfonyl group; amino group; methylamino group, ethylamino Mono-C1-C6 alkylamino groups such as propylamino groups; di-C1-C6 alkylamino groups such as dimethylamino groups and diethylamino groups; acylamino groups such as acetylamino groups and benzoylamino groups; phenylamino groups, 4-methyl An unsubstituted or substituted phenylamino group such as a phenylamino group; —N═C (CH ₃ ) OC ₂ H ₅ , —N═C (CF ₃ ) O (cPr) (cPr represents a cyclopropyl group). -N = C (OH) O (CH = CH ₂ ), -N = C (SCH ₃ ) OPh (Ph represents a phenyl group, the same applies hereinafter), etc. A group represented by (R ₃ ) OR ₄ ; —C (═O) N (CH ₃ ) C ₂ H ₅ , —C (═O) N (CF ₃ ) Ph, —C (═O) N (cPr ) Groups represented by —C (═O) N (R ₃ ) (R ₄ ) such as C ₂ H ₅ , —C (═O) N (CH═CH ₂ ) OH; —CO ₂ CH ₃ , — Groups represented by —CO ₂ R ₃ such as CO ₂ CCl ₃ , —CO ₂ Ph, —CO ₂ (cPr); —C (═S) N (CH ₃ ) C ₂ H ₅ , —C (═S ) N (CF ₃ ) Ph, —C═S) N (cPr) C ₂ H ₅ , —C (═S) N (CH═CH ₂ ) OH, etc. —C (═S) N (R ₃ ) ( group represented by R _4); -Si (CH _{3 3, -SiPh 3, -Si (cPr} ) 3, -Si (CH 3) 2 (t-Bu) (t-Bu is the same. At. Below represents the tertiary butyl group) -Si such _{(R 5} ) Groups represented by (R ₆ ) (R ₇ ); unsubstituted phenyl group, 4-methylphenyl group, 2-fluorophenyl group, 2,4-dichlorophenyl group, 2,4,6-trimethylphenyl group, etc. Or a phenyl group having a substituent; or an unsubstituted or substituted heterocyclic group.

R ₃ and R ₄ are each independently a hydrogen atom; a C1-C12 alkyl group such as a methyl group or an ethyl group; a C1-C12 haloalkyl group such as a trifluoromethyl group or a pentafluoroethyl group; a cyclopropyl group or a cyclopentyl group A C3-C12 cycloalkyl group such as a cyclohexyl group; a C2-C12 alkenyl group such as a vinyl group or an allyl group; a C2-C12 haloalkenyl group such as a 3-chloroallyl group; a C2 such as a propargyl group or a 3-butynyl group; C12 alkynyl group; C2-C12 haloalkynyl group such as 2-chloroethynyl group, 2-bromoethynyl group, 3,3,3-trifluoro-1-propynyl group; C1-C12 alkylthio group such as methylthio group and ethylthio group Hydroxyl group; C1-C12 alkoxy group such as methoxy group and ethoxy group; amino group; A mono C1-C6 alkylamino group such as a dimethylamino group or a diethylamino group; an acylamino group such as an acetylamino group or a benzoylamino group; a phenylamino group; A phenylamino group having an unsubstituted or substituted group such as a methylphenylamino group; or a phenyl having an unsubstituted or substituted group such as a phenyl group, a 4-methylphenyl group, a 2-chlorophenyl group, or a 2,4-difluorophenyl group; Group represents an unsubstituted or substituted heterocyclic group.

R _{5 to} R ₇ are each independently a hydrogen atom; a C1-C12 alkyl group such as a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a t-butyl group; or a phenyl group, An unsubstituted or substituted phenyl group such as a 4-methylphenyl group is represented.

  The heterocyclic group for Y is not particularly limited as long as it is a heterocyclic group containing at least one hetero atom in the ring. Here, examples of the hetero atom include a nitrogen atom, an oxygen atom, and a sulfur atom. The number of atoms constituting the ring of the heterocyclic group is preferably 3 to 8, more preferably 5 or 6. Furthermore, the heterocyclic group may be a saturated heterocyclic group or an unsaturated heterocyclic group, but an unsaturated heterocyclic group is preferable in terms of having excellent pest control activity. An unsaturated nitrogen-containing heterocyclic group is more preferable.

  Examples of such an unsaturated nitrogen-containing heterocyclic group include heterocyclic groups containing 1 to 3 nitrogen atoms in the ring and optionally 1 or 2 oxygen atoms or sulfur atoms. It is done.

  Specific examples of the unsaturated nitrogen-containing heterocyclic group include pyrrol-2-yl group, pyrrol-3-yl group, pyrazol-3-yl group, pyrazol-4-yl group, oxazol-2-yl group, and oxazole. -4-yl group, oxazol-5-yl group, thiazol-2-yl group, thiazol-4-yl group, thiazol-5-yl group, isoxazol-4-yl group, isoxazol-5-yl group, Isothiazol-2-yl group, isothiazol-4-yl group, isothiazol-5-yl group, triazol-3-yl group, triazol-5-yl group, 1,3,4-oxadiazole-2- Yl group, 1,2,4-oxadiazol-3-yl group, 1,2,4-oxadiazol-5-yl group, 1,3,4-thiadiazol-2-yl group, 1,2,4 4-thiadiazo -3-yl group, 1,2,4-thiadiazol-5-yl 5-membered unsaturated nitrogen-containing heterocyclic ring group such as a group;

  Pyridin-2-yl group, Pyridin-3-yl group, Pyridin-4-yl group, Pyridazin-3-yl group, Pyridazin-4-yl group, Pyrimidin-2-yl group, Pyrimidin-4-yl group, Pyrimidine 6-membered unsaturated nitrogen-containing heterocyclic group such as -5-yl group, pyrazin-2-yl group and triazin-2-yl group.

  The heterocyclic group may have a substituent at any position. Such substituents include: cyano group; nitro group; formyl group; halogen atom such as fluorine atom, chlorine atom and bromine atom; C1-C6 alkyl group such as methyl group, ethyl group, n-propyl group and isopropyl group; C1-C6 alkoxy group such as ethoxy group; C3-C8 cycloalkyl group such as cyclopropyl group, cyclopentyl group, cyclohexyl group; C3-C8 cycloalkyloxy such as cyclopropyloxy group, cyclopentyloxy group, cyclohexyloxy group Group: C3-C8 cycloalkyl C1-C6 alkyl group such as cyclopropylmethyl group, cyclopentylmethyl group, cyclohexylmethyl group; C3-C8 cycloalkyl C1-C6 alkoxy such as cyclopropylmethoxy group, cyclopentylmethoxy group, cyclohexylmethoxy group, etc. Base C2-C6 alkenyloxy groups such as pentenyloxy group and butenyloxy group; C1-C6 haloalkyl groups such as trifluoromethyl group and pentafluoroethyl group; C1-C6 haloalkoxy groups such as trifluoromethoxy group and pentafluoroethoxy group; C2-C6 haloalkenyloxy groups such as chloropropenyloxy group and chlorobutenyloxy group; C1-C6 alkoxycarbonyl groups such as methoxycarbonyl group and ethoxycarbonyl group (alkoxycarbonyl having 1 to 6 carbon atoms in the alkoxy moiety) Meanings of a group, the same applies hereinafter); a phenyl group having a non-substituted or substituted group such as a phenyl group, a 4-methylphenyl group, and a 2-chlorophenyl group;

  n represents an integer of 0 to 4. When n is 2 or more, the plurality of Y may be the same as or different from each other.

When two Ys are adjacent to each other, the two Ys are bonded together to form —CH ₂ CH ₂ CH ₂ —, —CH ₂ CH ₂ O—, —CH ₂ OCH ₂ —, —OCH. ₂ O—, —CH ₂ CH ₂ S—, —CH ₂ SCH ₂ , —SCH ₂ S—, —CH ₂ CH ₂ CH ₂ CH ₂ —, —CH ₂ CH ₂ CH ₂ O—, —CH ₂ CH _{2 OCH 2 -, - CH 2 OCH} 2 O -, - OCH 2 CH 2 O -, - OCH 2 CH 2 S -, - SCH 2 CH 2 S -, - OCH = N -, - forming a SCH = N-like By doing so, you may form a 5-membered ring or a 6-membered ring with the carbon atom to which each of two Y couple | bonds.

  At this time, the hydrogen atom bonded to each carbon atom forming the ring may be substituted by a substituent T. Further, when simultaneously substituted by two or more T, each T is the same as each other Or they may be different.

  Here, T is a cyano group, nitro group, formyl group, halogen atom, C1-C6 alkyl group, C1-C6 alkoxy group, C3-C8 cycloalkyl group, C3-C8 cycloalkyloxy group, C3-C8 cycloalkyl. C1-C6 alkyl group, C3-C8 cycloalkyl C1-C6 alkoxy group, C2-C6 alkenyloxy group, C1-C6 haloalkyl group, C1-C6 haloalkoxy group, C2-C6 haloalkenyloxy group, C1-C6 alkoxycarbonyl Group, unsubstituted or substituted phenyl group; and the like. Specific examples thereof are the same as those exemplified as the substituent for the heterocyclic group of Y.

Q is hydrogen atom; halogen atom; cyano group; formyl group; oxo group (= O); C1-C12 alkyl group; C2-C6 alkenyl group; C2-C6 alkynyl group; C1-C12 haloalkyl group; Alkyl group; C3-C8 halocycloalkyl group; hydroxyl group; C1-C6 alkoxy group; C1-C6 haloalkoxy group; C1-C6 alkylsulfonyloxy group; unsubstituted or substituted phenylsulfonyloxy group; mercapto group; -C6 alkylthio group; C1-C6 alkylsulfenyl group; C1-C6 alkylsulfonyl group; C1-C6 haloalkylthio group; C1-C6 haloalkylsulfenyl group; C1-C6 haloalkylsulfonyl group; unsubstituted or substituted phenylthio Group; unsubstituted or substituted Phenylsulfonyl group; unsubstituted or substituted phenylsulfonyl group; amino group; mono-C1 to C6 alkylamino group; di-C1 to C6 alkylamino group; acylamino group; phenylamino group having no substituent or substituent; A group represented by —C (═O) R ₈ such as C (═O) CH ₃ , —C (═O) CF ₃ , —C (═O) Ph, —C (═O) cPr; _{2 CH 3, -CO 2 CCl 3} , -CO 2 Ph, a group represented by _-CO 2 _{R 8,} such as _{-CO 2 (cPr); -OC (} = O) CH 3, -OC (= O) CF ₃ , groups represented by —OC (═O) R ₈ such as —OC (═O) Ph, —OC (═O) cPr; —C (═O) SCH ₃ , —C (═O) SCCl ₃ Table with -C (= O) SPh, -C (= O) -C such S (cPr) (= O) SR 8 Is the _{group; -C (= S) OCH 3} , -C (= S) OCCl 3, -C (= S) OPh, -C (= S) O (cPr) like the -C (= S) OR ₈ -C (= S) SCH ₃ , -C (= S) SCCl ₃ , -C (= S) SPh, -C (= S) S (cPr) and the like -C (= S) groups represented by _{SR 8; -C (= S)} NHCH 3, -C (= S) N (CH 3) 2, -C (= S) NHPh, -C (= S) NH (cPr) such _{-C (= S) N (R} 8) group represented by _{(R 9); -N = C} (CH 3) OC 2 H 5, -N = C (CF 3) O (cPr), - N = Groups represented by —N═C (R ₈ ) OR ₉ such as C (OH) O (CH═CH ₂ ) and —N═C (SCH ₃ ) OPh; —C (═O) NHCH ₃ , —C _{(= O) N (CH 3} ) 2, -C (= O) NHPh -C (= O) NH (cPr ) like the -C _{(= O) N (R 8} ) group represented by _{(R 9); -Si (CH} 3) 3, -SiPh 3, -Si (cPr) ₃ , a group represented by —Si (R ₁₀ ) (R ₁₁ ) (R ₁₂ ), such as —Si (Me) ₂ (t-Bu); a phenyl group having no substituent or a substituent; Represents a heterocyclic group having a substituent.

  Halogen atom, C2-C6 alkenyl group, C2-C6 alkynyl group, C3-C8 cycloalkyl group, C3-C8 halocycloalkyl group, C1-C6 alkoxy group, C1-C6 haloalkoxy group, C1-C6 Alkylsulfonyloxy group, unsubstituted or substituted phenylsulfonyloxy group, C1-C6 alkylthio group, C1-C6 alkylsulfenyl group, C1-C6 alkylsulfonyl group, C1-C6 haloalkylthio group, C1-C6 haloalkylsulfur group Phenyl group, C1-C6 haloalkylsulfonyl group, unsubstituted or substituted phenylthio group, unsubstituted or substituted phenylsulfenyl group, unsubstituted or substituted phenylsulfonyl group, amino group, mono C1-C6 Alkylamino group, di-C ~C6 alkyl amino group, an acylamino group, specific examples of the phenyl group which carries an unsubstituted or substituted groups include the same ones as exemplified as specific examples of these groups of said Y.

Specific examples of the C1-C12 alkyl group and the C1-C12 haloalkyl group of Q include those similar to those exemplified as the C1-C12 alkyl group and the C1-C12 haloalkyl group of R ₃ and R _4. .

R ₈ and R ₉ are each independently the same as R ₃ and R ₄ , hydrogen atom, C1-C12 alkyl group, C1-C12 haloalkyl group, C3-C12 cycloalkyl group, C2-C12 alkenyl group, C2 -C12 haloalkenyl group, C2-C12 alkynyl group, C2-C12 haloalkynyl group, C1-C12 alkylthio group, hydroxyl group, C1-C12 alkoxy group, amino group, mono C1-C6 alkylamino group, di-C1-C6 alkylamino A group, an acylamino group, an unsubstituted or substituted phenylamino group, or an unsubstituted or substituted phenyl group.

R _{10 to} R ₁₂ each independently represent a hydrogen atom, a C1 to C12 alkyl group, a C1 to C12 haloalkyl group, or an unsubstituted or substituted phenyl group similar to R ₃ and R _4. .

q represents an integer of 0 to 7.
When q is 2 or more, the plurality of Q may be the same as or different from each other.

  Z represents an unsubstituted or substituted phenyl group, or an unsubstituted or substituted heterocyclic group. Specific examples thereof are the same as those listed as specific examples of the phenyl group having an unsubstituted or substituted group and the heterocyclic group having an unsubstituted or substituted group. Specific examples of Z include those shown in the following (Z-1) to (Z-32), but are not limited thereto.

  In the above formula, r is a halogen atom such as fluorine atom, chlorine atom or bromine atom; cyano group; nitro group; C1-C6 alkyl group such as methyl group or ethyl group; cyclopropyl group, cyclopentyl group, cyclohexyl group, etc. C3-C8 cycloalkyl group; C2-C6 alkenyl group such as vinyl group and propenyl group; C2-C6 alkynyl group such as ethynyl group and propargyl group; hydroxyl group; C1-C6 alkoxy such as methoxy group, ethoxy group and isopropoxy group Groups: unsubstituted or substituted phenoxy groups such as phenoxy group and 4-methylphenoxy group; mercapto groups; C1-C6 alkylthio groups such as methylthio group and ethylthio group; C1-C6 such as methylsulfinyl group and ethylsulfinyl group Alkylsulfinyl group; methylsulfonyl group, ethylsulfonyl group, etc. 1-C6 alkylsulfonyl group; phenylthio group having an unsubstituted or substituted group such as phenylthio group and 4-chlorophenylthio group; phenylsulfonyl group having an unsubstituted or substituted group such as phenylsulfonyl group and 4-methylphenylsulfonyl group; C1-C6 alkylsulfonyloxy groups such as methylsulfonyloxy group and ethylsulfonyloxy group; phenylsulfonyloxy groups having unsubstituted or substituted groups such as phenylsulfonyloxy group and 2-chlorophenylsulfonyloxy group; methoxycarbonyl group, ethoxycarbonyl A C1-C6 alkoxycarbonyl group such as a group;

m0 represents an integer of 0 to 5, m1 represents an integer of 0 to 4, m2 represents an integer of 0 to 3, m3 represents an integer of 0 to 2, and m4 represents 0 or 1. When m0 to m3 are each 2 or more, a plurality of r may be the same or different from each other.
r ′ represents a hydrogen atom; a C1-C6 alkyl group such as a methyl group or an ethyl group; an unsubstituted or substituted phenyl group such as a phenyl group or a 4-methylphenyl group;

R ₁ and R ₂ are each independently a hydrogen atom; a cyano group; optionally substituted by G (C1-C12 alkyl group; C3-C12 cycloalkyl group; C2-C12 alkenyl group; C3-C12 cycloalkenyl) A C2-C12 alkynyl group; a mercapto group; a C1-C6 alkylthio group; a C1-C6 alkylsulfonyl group; an unsubstituted or substituted phenylthio group; an unsubstituted or substituted phenylsulfonyl group; -SNH (CH ₃ ), —SN (CH ₃ ) ₂ , —SNHPh, —SNH (cPr) and the like, —SN (R ₁₃ ) (R ₁₄ ) groups; —SO ₂ NH (CH ₃ ), —SO ₂ N ( _{CH 3) 2, -SO 2 NHPh} , group represented by _-S such _{-SO 2 NH (cPr) (O} ) 2 N (R 13) (R 14); a hydroxyl group; main . Dimethylvinylsiloxy groups trifluoromethoxy group, a phenoxy group, cyclopentyl group represented by -OR _13, such as a group; an amino group, methylamino group, ethylamino group, phenylamino group, dimethylamino group, -N such diethylamino group A group represented by (R ₁₃ ) (R ₁₄ ); —N═CH (CH ₃ ), —N═CH (CF ₃ ), —N═CH (Ph), —N═CH (cPr), etc. A group represented by N═CH (R ₁₃ ); —N═C (CH ₃ ) ₂ , —N═C (CH ₃ ) (CF ₃ ), —N═C (CF ₃ ) ₂ , —N═C A group represented by —N═C (R ₁₃ ) (R ₁₄ ) such as (CH ₃ ) (Ph), —N═C (Ph) ₂ , —N═C (CH ₃ ) (cPr); _{(= O) CH 3, -C} (= O) CF 3, -C (= O) Ph, -C (= O) cPr like the -C (= O Group represented by _{R 13; -CO 2 CH 3,} -CO 2 CCl 3, -CO 2 Ph, a group represented by _-CO 2 _{R 13,} such as _{-CO 2 cPr; -C (= O} ) SCH 3 A group represented by —C (═O) SR ₁₃ such as —C (═O) SCCl ₃ , —C (═O) SPh, —C (═O) S (cPr); —C (═O) N (R ₁₃ ) (R ₁₄ ) such as NHCH ₃ , —C (═O) N (CH ₃ ) ₂ , —C (═O) NHPh, —C (═O) NH (cPr) groups represented _{by); -C (= S) OCH} 3, -C (= S) OCCl 3, -C (= S) OPh, -C (= S) O (cPr) like the -C (= S ) OR ₁₃ group; -C (= S) SCH ₃ , -C (= S) SCCl ₃ , -C (= S) SPh, -C (= S) S (cPr) and the like -C ( = S) groups represented by _{SR 13 -C (= S) NHCH 3,} -C (= S) N (CH 3) 2, -C (= S) NHPh, -C (= S) -C such NH (cPr) (= S) N ( R _{13) (groups} represented by _{R 14); -C (= NH} ) OCH 3, -C (= NCH 3) OCH 3, -C (= NH) OCCl 3, -C (= NH) OPh, - _{C (= NCH 3) OPh,} -C (= NH) -C such OcPr ₍₌ NR 13) group represented by _{OR 14; -C (= NH)} SCH 3, -C (= NCH 3) SCH 3 , -C (= NH) SCCl ₃ , -C (= NH) SPh, -C (= NCH ₃ ) SPh, -C (= NH) ScPr and the group represented by -C (= NR ₁₃ ) SR _{14 ; -C (= NH) NHCH 3} , -C (= NCH 3) NHCH 3, -C (= NH) N (CH 3) 2, -C (= NH) NHPh, -C (= Phenyl group having unsubstituted or _{substituted;; CH 3) NHPh, -C} (= NH) NH (-C (= NR 13) N (R 14) ( groups represented by _{R 15)} of cPr) or the like, Or an unsubstituted or substituted heterocyclic group;

R _{13 to} R ₁₅ are each independently the same as R ₃ and R ₄ , hydrogen atom, C1-C12 alkyl group, C1-C12 haloalkyl group, C3-C12 cycloalkyl group, C2-C12 alkenyl group, C2 -C12 haloalkenyl group, C2-C12 alkynyl group, C2-C12 haloalkynyl group, C1-C12 alkylthio group, hydroxyl group, C1-C12 alkoxy group, amino group, mono C1-C6 alkylamino group, di-C1-C6 alkylamino A group, an acylamino group, an unsubstituted or substituted phenylamino group, or an unsubstituted or substituted phenyl group.

Wherein _{R 1} and _{R 2,} as the C1~C12 alkyl group substituted C1~C12 may alkyl group by G, a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, t- butyl group, A pentyl group, a hexyl group, an octyl group, a nonyl group, a decyl group, etc. are mentioned.

  Examples of the C3-C12 cycloalkyl group of the C3-C12 cycloalkyl group optionally substituted by G include a cyclopropyl group, a cyclopentyl group, a cyclohexyl group, a cyclooctyl group, and the like.

  As the C2-C12 alkenyl group of the C2-C12 alkenyl group optionally substituted by G, vinyl group, propenyl group, 2-butenyl group, 3-butenyl group, 2-pentenyl group, 3-pentenyl group, 4- Examples thereof include a pentenyl group, a 2-hexenyl group, a 3-hexenyl group, a 4-hexenyl group, and a 5-hexenyl group.

  Examples of the C3-C12 cycloalkenyl group of the C3-C12 cycloalkenyl group optionally substituted by G include a cyclopentenyl group, a cyclohexenyl group, a cyclooctenyl group, and the like.

  Examples of the C2-C12 alkynyl group of the C2-C12 alkynyl group optionally substituted by G include ethynyl group, propargyl group, 2-butynyl group, 2-pentynyl group and the like.

G is a halogen atom; a cyano group; a nitro group; a C3-C8 cycloalkyl group; a C3-C8 halocycloalkyl group; a hydroxyl group; a C1-C6 alkoxy group; a C1-C6 alkylsulfonyloxy group; Phenylsulfonyloxy group; mercapto group; C1-C6 alkylthio group; C1-C6 alkylsulfenyl group; C1-C6 alkylsulfonyl group; C1-C6 haloalkylthio group; C1-C6 haloalkylsulfenyl group; C1-C6 haloalkylsulfonyl group An unsubstituted or substituted phenylthio group; an unsubstituted or substituted phenylsulfenyl group; an unsubstituted or substituted phenylsulfonyl group; a methoxy group, an ethoxy group, a trifluoromethoxy group, a cyclopropyloxy group; Allyloxy , 3-chloro-allyloxy group, propargyloxy group, 3-chloro-propargyloxy group, a group represented by -OR _16, such as a phenoxy group; an amino group, methylamino group, phenylamino group, dimethylamino group, diphenylamino group A group represented by —N (R ₁₆ ) (R ₁₇ ) such as a phenylmethylamino group; —N═CH (CH ₃ ), —N═CH (CF ₃ ), —N═CHPh, —N═CH Groups represented by —N═CH (R ₁₆ ) such as (cPr); —N═C (CH ₃ ) ₂ , —N═C (CH ₃ ) (CF ₃ ), —N═C (CF ₃ ) ₂ , a group represented by —N═C (R ₁₆ ) (R ₁₇ ) such as —N═C (Ph) ₂ , —N═C (CH ₃ ) Ph, —N═C (cPr) ₂ ; _{C (= O) CH 3,} -C (= O) CF 3, -C (= O) Ph, -C (= O) -C such cPr = _O) group represented by _{R 16; -CO 2 CH 3,} -CO 2 CCl 3, -CO 2 Ph, a group represented by _-CO 2 _{R 16,} such as -CO 2 (cPr); -C ( Groups represented by —C (═O) SR ₁₆ such as —O) SCH ₃ , —C (═O) SCCl ₃ , —C (═O) SPh, —C (═O) S (cPr); —C (═O) N (R ₁₆ ) (C (═O) NHCH ₃ , —C (═O) N (CH ₃ ) ₂ , —C (═O) NHPh, —C (═O) NHcPr, etc. A group represented by R ₁₇ ); —C (═S) OCH ₃ , —C (═S) OCCl ₃ , —C (═S) OPh, —C (═S) O (cPr) and the like —C ( = S) a group represented by OR ₁₆ ; -C (= S) SCH ₃ , -C (= S) SCCl ₃ , -C (= S) SPh, -C (= S) S (cPr)- It is represented by C (= S) _{SR 16 Group; -C (= S) NHCH 3} , -C (= S) N (CH 3) 2, -C (= S) NHPh, -C (= S) NHcPr like _{-C (= S) N (R} 16 ) _(group represented by _{R 17); -C (= NH} ) OCH 3, -C (= NCH 3) OCH 3, -C (= NH) OCCl 3, -C (= NH) OPh, -C ( Groups represented by —C (═NR ₁₆ ) OR ₁₇ such as —NCH ₃ ) OPh and —C (═NH) OcPr; —C (═NH) SCH ₃ , —C (═NCH ₃ ) SCH ₃ , — represented by _{C (= NH) SCCl 3,} -C (= NH) SPh, -C (= NCH 3) SPh, -C (= NH) -C such _{S (cPr) (= NR 16} ) SR 17 _{group; -C (= NH) NHCH 3} , -C (= NCH 3) NHCH 3, -C (= NH) N (CH 3) 2, -C (= NH) NHPh, C (= NH) _-C such _{NHcPr (= NR 16) N (} R 17) group represented by _{(R 18); -Si (CH} 3) 3, -SiPh 3, -Si (cPr) 3, - A group represented by —Si (R ₁₉ ) (R ₂₀ ) (R ₂₁ ) such as Si (Me) ₂ (t-Bu); an unsubstituted or substituted phenyl group; or an unsubstituted or substituted group The heterocyclic group which has;

Here, R _{16 to} R ₁₈ are each independently a hydrogen atom, a C1 to C12 alkyl group, a C1 to C12 haloalkyl group, a C3 to C12 cycloalkyl group, or a C2 to C12 alkenyl, which is the same as R ₃ and R _4. Group, C2-C12 haloalkenyl group, C2-C12 alkynyl group, C2-C12 haloalkynyl group, C1-C12 alkylthio group, hydroxyl group, C1-C12 alkoxy group, amino group, mono C1-C6 alkylamino group, di-C1- A C6 alkylamino group, an acylamino group, an unsubstituted or substituted phenylamino group, or an unsubstituted or substituted phenyl group is represented.

R _{19 to} R ₂₁ each independently represent a hydrogen atom, a C1 to C12 alkyl group, a C1 to C12 haloalkyl group, or an unsubstituted or substituted phenyl group similar to R ₃ and R _4. .

  Specific examples of the heterocyclic group having an unsubstituted or substituted group of G include the same as those listed as specific examples of the heterocyclic group having an unsubstituted or substituted group of Y.

C ₁ -C 6 alkylthio group, C ₁ -C 6 alkylsulfonyl group, unsubstituted or substituted phenylthio group, unsubstituted or substituted phenylsulfonyl group, C 1 -C 6 alkoxy group, mono C ₁ of R ₁ and R ₂ -C6 alkylamino group, di-C1-C6 alkylamino group, acylamino group, unsubstituted or substituted phenylamino group, unsubstituted or substituted phenyl group, and unsubstituted or substituted heterocyclic group Specific examples of Y include a C1-C6 alkylthio group, a C1-C6 alkylsulfonyl group, an unsubstituted or substituted phenylthio group, an unsubstituted or substituted phenylsulfonyl group, a C1-C6 alkoxy group, a mono C1-C6 alkylamino group, di-C1-C6 alkylamino group Acylamino group, a phenyl group which carries an unsubstituted or substituted group, phenyl group an unsubstituted or substituted, and include the same ones listed as specific examples of the heterocyclic group having unsubstituted or substituted.

R ₁ and R ₂ are bonded together to form a group represented by ═C (R ₁₃ ) (R ₁₄ ) (R ₁₃ and R ₁₄ have the same meaning as described above). Alternatively, R ₁ and R ₂ may be bonded together to form a 3- to 8-membered ring.

Specific examples of the group represented by ═C (R ₁₃ ) (R ₁₄ ) include ═CH ₂ , ═CH (CH ₃ ), ═C (CH ₃ ) ₂ , ═CH (C ₆ H ₅ ), = C (C ₆ H ₅ ) _{2 and the} like can be mentioned, but not limited thereto.

Specific examples of the 3-8 membered ring and _{R 1} and _{R 2} are formed by bonding together, _{R 1} and _{R 2} and is - to form a C2~C7 alkylene chain turned cord And a 3- to 8-membered ring constituted with a nitrogen atom to be bonded.

At this time, the alkylene chain may contain one oxygen atom, sulfur atom or nitrogen atom, and is a halogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C1-C6 alkoxy (C1-C6) alkyl group, It may be substituted by a C1-C6 alkoxy group, a formyl group, a C1-C6 alkylcarbonyl group, a C1-C6 haloalkylcarbonyl group, or a C1-C6 alkoxycarbonyl group.
s represents 0 or 1.

  As the nitrogen-containing heterocyclic compound of the present invention, the following formula (I-1)

(Wherein W, A ₁ , A ₂ , A ₃ , Y, n, R ₁ , R ₂ , X, Q, and Z have the same meanings as described above). Preferably there is a formula (I-2)

(Wherein A ₁ , A ₂ , A ₃ , Y, n, R ₁ , R ₂ , X, Q, and Z represent the same meaning as described above). Is particularly preferred.

The compound represented by the formula (I) can be produced, for example, by the method shown below.
(Production method 1)

Wherein W, A ₁ , A ₂ , A ₃ , Y, n, R ₁ , R ₂ , X, Q, q and Z represent the same meaning as described above, L is a halogen atom, C1 to C6 Alkoxy group, phenoxy group, C1-6 alkylcarbonyloxy group, C1-C6 alkoxycarbonyloxy group, 1-imidazolyl group, 1-pyrazolyl group, p-toluenesulfonyloxy group, methanesulfonyloxy group, trifluoromethanesulfonyl group, etc. Represents a leaving group.)

  That is, the compound represented by the formula (1) and the amine compound represented by the formula (3) are reacted by using a condensing agent in the presence of a base as desired, thereby being represented by the formula (4). A compound can be obtained.

  As the condensing agent used in this reaction, Mukaiyama reagent (2-chloro-N-methylpyridinium iodide), DCC (1,3-dicyclohexylcarbodiimide), EDCI (1-ethyl-3- (3-dimethylaminopropyl)- Carbodiimide hydrochloride), carbonyldiimidazole, dimethylpropynylsulfonium bromide, propargyltriphenylphosphonium bromide, diethyl cyanophosphate and the like.

  Examples of the base used include alkali metal hydroxides such as sodium hydroxide and potassium hydroxide; carbonates such as sodium carbonate and potassium carbonate; metal alkoxides such as sodium methoxide, potassium t-butoxide and magnesium ethoxide; n-butyl Organic metals such as lithium and lithium diisopropylamide (LDA); metal hydrides such as sodium hydride and potassium hydride; organic bases such as triethylamine, diisopropylethylamine, pyridine and N, N-dimethylaminopyridine; and the like.

The solvent to be used is not particularly limited as long as it is an inert solvent for the reaction. For example, hydrocarbon solvents such as pentane, hexane, heptane, benzene, toluene, xylene; halogen solvents such as dichloromethane, 1,2-dichloroethane, chloroform, carbon tetrachloride; nitrile solvents such as acetonitrile, propionitrile; Ether solvents such as diethyl ether, dioxane and tetrahydrofuran; aprotic polar solvents such as N, N-dimethylformamide (DMF) and dimethyl sulfoxide (DMSO); and a mixed solvent obtained by mixing two or more of these solvents; Is mentioned.
The reaction proceeds smoothly in a temperature range from −78 ° C. to the boiling point of the solvent used.

  In addition, the compound represented by the formula (4) is a method in which the compound represented by the formula (1) is reacted with a halogenating agent such as thionyl chloride or oxazolyl chloride; organic such as pivaloyl chloride or ethyl chloroformate After obtaining a compound represented by the formula (2) by a method of reacting with a halogen compound in the presence of a base if necessary; or a method of reacting with a carbonylimidazole or the like; The compound represented by Formula (4) can also be obtained by making it react with the compound represented with presence of a base if necessary.

  Examples of the base used in this reaction include alkali metal hydroxides such as sodium hydroxide and potassium hydroxide; carbonates such as sodium carbonate and potassium carbonate; metal alkoxides such as sodium methoxide, potassium t-butoxide and magnesium ethoxide; Organic metals such as n-butyllithium and lithium diisopropylamide (LDA); metal hydrides such as sodium hydride and potassium hydride; organic bases such as triethylamine, diisopropylethylamine, pyridine and N, N-dimethylaminopyridine; Can be mentioned.

  Solvents that can be used are not particularly limited as long as they are inert to the reaction. For example, hydrocarbon solvents such as pentane, hexane, heptane, benzene, toluene, xylene; dichloromethane, 1,2-dichloroethane, chloroform, four Halogen solvents such as carbon chloride; nitrile solvents such as acetonitrile and propionitrile; ether solvents such as diethyl ether, dioxane and tetrahydrofuran; non-protons such as N, N-dimethylformamide (DMF) and dimethyl sulfoxide (DMSO) Polar solvents; and mixed solvents obtained by mixing two or more of these solvents.

The reaction proceeds smoothly in a temperature range from −78 ° C. to the boiling point of the solvent used.
(Production method 2)

Wherein W, A ₁ , A ₂ , A ₃ , Y, n, R ₁ , R ₂ , X, Q, q and Z represent the same meaning as described above, Y ₁ represents a halogen atom, C _1- Represents a leaving group such as a ₆ haloalkylsulfonyloxy group or a C _1-6 alkylsulfonyloxy group.)

That is, the compound represented by the formula (5) and the compound represented by the formula (6) are subjected to a cross-coupling reaction using a general transition metal catalyst such as palladium described in the literature, for example, Tetrahedron Lett. 1997, 38, 36, 6359; Org. Chem. , 2000, 65, 4, 1144, etc., the compound represented by the formula (4) can be obtained by reacting according to the reaction conditions described in the above.
(Production method 3)

Wherein W, A ₁ , A ₂ , A ₃ , Y, n, Y ₁ , X, Q, q and Z are as defined above, Y ₁ is a halogen atom, C _1-6 haloalkylsulfonyl And represents a leaving group such as an oxy group or a C _1-6 alkylsulfonyloxy group, and R ₅ represents a lower alkyl group such as a methyl group or an ethyl group.)

  That is, the compound represented by the formula (7) and the compound represented by the formula (6) are subjected to a cross-coupling reaction using a general transition metal catalyst such as palladium described in literature, for example, Tetrahedron Lett. 1997, 38, 36, 6359; Org. Chem. , 2000, 65, 4, 1144, etc., the compound represented by the formula (8) can be obtained by reacting according to the reaction conditions described in the above.

Further, the compound represented by the formula (1) is obtained by reacting the compound represented by the formula (8) with a general ester hydrolysis reaction described in literatures, for example, J. Org. Am. Chem. Soc. , 1929, 51, 1865; Angew. Chem. , 1950, 63, 329 and the like.
(Production Method 4)

  Further, among the compounds of the present invention, a compound in which s is 1 in the formula (I) is an oxidant in a compound (a compound represented by the formula (4)) in which s is 0 in the formula (I). Can be obtained by acting.

  Examples of the oxidizing agent that can be used include hydrogen peroxide, peracetic acid, m-chloroperbenzoic acid, and the like.

  Many of the compounds represented by the formula (6), which are starting materials, are known substances and can be produced by known methods. For example, the compound represented by the formula (6-1) can be produced according to the reaction scheme shown below.

(Wherein Q and Z represent the same meaning as described above, and E represents a protecting group such as a benzyl group, a t-butoxycarbonyl group, an acetyl group or a benzoyl group.)

  That is, the compound represented by the formula (11) is reacted with the compound represented by the formula (10) in an appropriate solvent in the presence of an acid catalyst to thereby convert the compound represented by the formula (11). After being obtained, E can be deprotected to obtain the target compound represented by the formula (1-1).

Examples of the acid catalyst used in this reaction include trifluoroacetic acid.
The usage-amount of an acid catalyst is 0.1-0.5 equivalent normally with respect to the compound represented by Formula (9).

The solvent used in this reaction is not particularly limited as long as it is an inert solvent for the reaction. For example, hydrocarbon solvents such as n-pentane, n-hexane, n-heptane, benzene, toluene, xylene; halogen solvents such as dichloromethane, 1,2-dichloroethane, chloroform, carbon tetrachloride; acetonitrile, propiononitrile, etc. Nitrile solvents of: ether solvents such as diethyl ether, dioxane, tetrahydrofuran (THF); aprotic polar solvents such as N, N-dimethylformamide (DMF), dimethyl sulfoxide (DMSO); and two of these solvents A mixed solvent comprising the above; and the like.
The usage-amount of a solvent is 1-100 ml normally with respect to 1 g of compounds represented by Formula (9).

The reaction temperature is usually in the temperature range from −20 ° C. to the boiling point of the solvent used.
The reaction time is usually several minutes to several tens of hours.

  The method for removing E from the compound represented by the formula (11) is not particularly limited, and a known reaction for removing an amino-protecting group can be applied. For example, a method of reacting a compound represented by formula (11) with chloroformic acid-1-chloroethyl ester; a method of hydrolyzing a compound represented by formula (11) using mineral acids such as hydrochloric acid; A method of hydrolyzing a compound represented by the formula (9) using an alkali such as sodium hydroxide, sodium sulfide or sodium disulfide; an alcoholysis of a compound represented by the formula (11) using a metal alkoxide And a method of reducing the compound represented by the formula (11) using a reducing agent such as lithium aluminum hydride or sodium borohydride.

  The solvent used in the method for desorbing E is not particularly limited as long as it is a solvent inert to the reaction. For example, hydrocarbon solvents such as n-pentane, n-hexane, n-heptane, benzene, toluene, xylene; halogen solvents such as dichloromethane, 1,2-dichloroethane, chloroform, carbon tetrachloride; acetonitrile, propiononitrile, etc. Nitrile solvents; ether solvents such as diethyl ether, dioxane and tetrahydrofuran (THF); aprotic polar solvents such as N, N-dimethylformamide (DMF) and dimethyl sulfoxide (DMSO); and two of these solvents A mixed solvent comprising the above; and the like. The usage-amount of a solvent is 1-100 ml normally with respect to 1 g of compounds represented by Formula (11).

The reaction temperature is usually in the temperature range from 0 ° C. to the boiling point of the solvent used.
The reaction time is usually several minutes to 24 hours.

  The salt of the compound represented by the formula (I) is not particularly limited as long as it is agriculturally and horologically acceptable. For example, salts of inorganic acids such as hydrochlorides, nitrates, sulfates and phosphates of the compounds represented by the formula (I); salts of organic acids such as acetic acid, propionic acid and lactic acid.

  The salt of the compound represented by the formula (I) can be produced, for example, by allowing an inorganic acid or an organic acid to act on the compound represented by the formula (I).

  In any reaction, after completion of the reaction, if purification of the product is necessary after the usual post-treatment operation, it is purified by a known and conventional purification means such as distillation, recrystallization or column chromatography. The target product can be isolated.

  The structure of the target product can be identified and confirmed by known analytical means such as elemental analysis, NMR spectrum, IR spectrum, and mass spectrum.

2) Pest control agents The compounds represented by formula (I) and salts thereof (hereinafter referred to as “the compounds of the present invention”) include agricultural pests, sanitary pests, storage pests, clothing pests, house pests, etc. It can be used for control, and has the effect of killing insects, nymphs, larvae and ovaries. Typical examples are as follows.

  Lepidopterous pests, for example, Spodoptera litura, Coleoptera, Tamanayaga, Aomushi, Tamanaginuwaba, Koga, Chanoko Kakumon Hamaki, Chahamaki, Momosinkiga, Nashihime Shinkii, Citrus Harmiga, Chanohosoga, Giant Pomera , Sugimadama, Heliotis, Helicoberpa, Agrotis, Iga, Kodlinga, Cottontail, etc.

Hemiptera pests, for example, peach aphid, cotton aphid, phantom aphid, wheat beetle aphid, hosohelamushi, aokusamemushi, agarine aphid, staghorn aphid, onitsu whitefly, tobacco whitefly, silver leaf whitefly, silver leaf whitefly, Gunby beetle, brown planthopper, Japanese brown planthopper, white-spotted planthopper, leafhopper, etc.
Coleopterous pests, for example, Kisodemi beetle, cucumber beetle, Colorado potato beetle, rice weevil, weevil, azuki beetle, beetle, scallop, diablotica, tobacco, scallop, slatinus, pine moth, Cotton weevil, etc.

Diptera pests, for example, houseflies, giant black flies, sentinic flies, fruit flies, citrus flies, fly flies, rice leaf flies, Drosophila melanogaster, sand flies, Aedes albopictus, Aedes aegypti, Aedes albopictus, etc.
Thrips-like pests, such as Thrips thrips, Thrips thrips,
Hymenopteran pests, for example, Himeari, Kirosuzubee, Bee, etc.
Straight-eyed pests, such as grasshopper, German cockroach, American cockroach, black cockroach, etc.

Termite pests, such as termites, Yamato termites,
Lepidoptera pests, for example, human fleas, cat fleas, etc., lice eye pests, for example, human lice,
Tick, for example, spider mite, spider mite, kanzawa spider mite, citrus spider mite, apple spider mite, citrus spider mite, apple spider mite, chano mite, brebipalpas spp.
Plant parasitic nematodes such as, for example, sweet potato nematode, nestle nematode, soybean cyst nematode, rice scented nematode, and pinewood nematode.

  Pests preferably applied are lepidopterous insects, semilepidopterous insects, mites, thrips insects, and coleopterous insects, and particularly preferably mites.

  In recent years, resistance to organophosphates, carbamates, and acaricides has developed in many pests such as Japanese pests, leafhoppers, leafhoppers, and aphids, resulting in insufficient efficacy of these drugs. Also effective drugs are desired. The compound of the present invention is an agent having an insecticidal and acaricidal effect that is excellent not only for susceptible strains, but also for pests resistant to organophosphates, carbamates, and pyrethroids, and mites that are resistant to acaricides.

The compound of the present invention is a highly safe drug with little phytotoxicity, low toxicity to fish and warm-blooded animals.
The compound of the present invention can also be used as an antifouling agent for preventing aquatic organisms from adhering to underwater contact objects such as ship bottoms and fish nets.

  Some compounds of the present invention exhibit bactericidal activity, herbicidal activity, and planting action. Some intermediate compounds of the compounds of the present invention exhibit insecticidal / miticidal activity.

The insecticide and acaricide of the present invention contain one or more compounds of the present invention as active ingredients.
When the compound of the present invention is actually applied, it can be used as it is without adding other components. Usually, however, it is further mixed with a solid carrier, liquid carrier, gaseous carrier, or impregnated with a base such as a porous ceramic plate or nonwoven fabric. In addition, if necessary, surfactants and other adjuvants may be added to form a general agricultural chemical for use as an agricultural chemical, that is, a wettable powder, granule, powder, emulsion, aqueous solvent, suspension. , Granulated wettable powder, flowable, aerosol, fumes, heat transpiration, smoke, poison bait, microcapsule, etc.

  Additives and carriers, if solids are intended, vegetable powders such as soybean grains, wheat flour, mineral fine powders such as diatomaceous earth, apatite, gypsum, talc, bentonite, pyrophyllite, clay, benzoic acid Organic and inorganic compounds such as soda, urea and mirabilite are used. For liquid dosage forms, use petroleum fractions such as kerosene, xylene, and solvent naphtha, cyclohexane, cyclohexanone, dimethylformamide, dimethyl sulfoxide, alcohol, acetone, methyl isobutyl ketone, mineral oil, vegetable oil, and water as solvents. Can be used as As the gaseous carrier used for the propellant, butane gas, LG, dimethyl ether and carbon dioxide gas can be used.

  Examples of the bait base include bait ingredients such as cereal flour, vegetable oil, sugar, crystalline cellulose, antioxidants such as dibutylhydroxytoluene and nordihydroguaiaretic acid, preservatives such as dehydroacetic acid, and children such as pepper. Pest-attracting fragrances such as anti-fouling agents for pets and pets, cheese fragrances, and onion fragrances can be used.

  In order to obtain a uniform and stable form in these preparations, a surfactant may be added if necessary. The surfactant is not particularly limited. For example, alkyl ether added with polyoxyethylene, higher fatty acid ester added with polyoxyethylene, sorbitan higher fatty acid ester added with polyoxyethylene, and polyoxyethylene added. Nonionic surfactants such as tristyrylphenyl ether, sulfates of alkylphenyl ethers added with polyoxyethylene, alkylnaphthalene sulfonates, polycarboxylates, lignin sulfonates, formaldehyde of alkyl naphthalene sulfonates Examples include condensates and copolymers of isobutylene-maleic anhydride.

  When the compound of the present invention is used as an agricultural pest control agent, the amount of the active ingredient in the preparation is 0.01 to 90% by weight, particularly preferably 0.05 to 85% by weight. Emulsions, suspensions, flowables, aqueous solvents, and granule wettable powders are diluted with water to a predetermined concentration. As a solution, suspension, or emulsion, powders and granules are directly applied to plants or soil. Used in a spraying method.

  In addition, when the compound of the present invention is used as a pest control agent for prevention of epidemics, emulsions, wettable powders, flowables and the like are diluted with water to a predetermined concentration before application, oils, aerosols, fumes, poison baits. Apply it as it is about anti-tick sheets.

  When the compound of the present invention is used as a pest control agent for control of animal ectoparasites in domestic animals such as cattle and pigs, and pets such as dogs and cats, the formulation of the compound of the present invention is usually known in veterinary medicine. Use this method. As the method, for example, for the purpose of systemic control, administration is performed by tablets, capsules, immersion liquid, feed mixing, suppositories, injection (intramuscular, subcutaneous, intravenous, intraperitoneal, etc.), etc. In the case of aiming at non-systemic control, a method of administering an oily or aqueous solution by spraying, pouring-on, dropping-on, etc., and The method of mounting | wearing the thing which shape | molded the resin formulation in appropriate shapes, such as a collar and an ear tag. In this case, the compound of the present invention is usually used at a ratio of 0.01 to 1000 mg per 1 kg of the host animal.

  In addition, it goes without saying that the compound of the present invention is sufficiently effective alone, but other pesticides, fungicides, insecticides / acaricides, herbicides, plant regulators, synergists, fertilizers, soil conditioners. These can be used in combination or in combination with one or more animal feeds.

  Representative examples of active ingredients such as bactericides, insecticides, acaricides, plant growth regulators and the like that can be used in combination with or in combination with the compounds of the present invention are shown below.

Fungicide:
Captan, Folpet, Thiuram, Diram, Dinebu, Manebu, Mancozeb, Propineb, Polycarbamate, Chlorotaronin, Quintozen, Captaphor, Iprodione, Prosaimidon, Fluorimide, Mepronil, Flutolanil, Penciclone, Oxycarboxyne, Focetylaluminum, Propamocurve, Triazimephone, Triadimenol, propiconazole, diclobutrazole, viteltanol, hexaconazole, microbutanyl, flusilazole, etaconazole, fluotrimazole, flutriaphene, penconazole, diniconazole, cyproconazole, phenalimol, triflumizole, prochloraz , Imazalyl, pefazoate, tridemorph, fenpropimorph, triphorin, butio , Pyriphenox, anilazine, polyoxin, metalaxyl, oxadixyl, furaxyl, isoprothiolane, probenazole, pyrrolnitrin, blasticidin S, kasugamycin, validamycin, dihydrostreptomycin sulfate, benomyl, carbendazim, thiophanate methyl, hymexazole, basic chlorination Copper, basic copper sulfate, fentin acetate, triphenyltin hydroxide, dietofencarb, quinomethionate, binapacryl, lecithin, baking soda, dithianon, dinocup, phenaminosulfur, dichromemedin, guazatine, dodin, IBP, edifenphos, mepanipyrim, fermzone, trichramide , Metasulfocarb, fluazinam, etokinolac, dimethomorph, pyroxylone, teclophthala , Fusalide, phenazine oxide, thiabendazole, tricyclazole, vinclozoline, simoxanyl, cyclobutanyl, guazatine, propamocarb hydrochloride, oxolinic acid, cyflufenamide, iminoctazine, cresoxime methyl, triazine, fenhexamide, cyazofamide, cyprodinil, prothioconazole, fenbuconazole, fenbuconazole Roxystrobin, azoxystrobin, hexaconazole, imibenconazole, tebuconazole, difenoconazole, quinomethionate, carpropamide, etc.

Insecticides and acaricides:
Organophosphorus and carbamate insecticides:
Fenthion, fenitrothion, diazinon, chlorpyrifos, ESP, bamidthione, phentoate, dimethoate, formothione, marathon, trichlorfone, thiometone, phosmet, dichlorvos, acephate, EPBP, methyl parathion, oxydimethone methyl, ethion, salicione, cyanophos, isoxathione, cyanophos, isoxathione Methidathion, sulfophos, chlorfenvinphos, tetrachlorvinphos, dimethylvinphos, propaphos, isofenphos, ethylthiomethone, propenofos, pyracrofos, monocrotophos, azinephosmethyl, aldicarb, mesomil, thiodicarb, carbofuran, carbosulfan, benfracarb, furiocarb, Propoxur, BPMC, M MC, MIPC, carbaryl, pirimicarb, ethiofencarb, fenoxycarb, cartap, thiocyclam, bensultap and the like.

Pyrethroid insecticides:
Permethrin, cypermethrin, deltamethrin, fenvalerate, fenpropatoline, pyrethrin, allethrin, tetramethrin, resmethrin, dimethrin, propraslin, phenothrin, protorin, fulvalinate, cyfluthrin, cyhalothrin, flucitrinate, etofenprox, cycloprotorin, tralomethrin , Silafluophene, acrinatrin, etc.

Benzoylurea and other insecticides:
Diflubenzuron, chlorfluazuron, hexaflumuron, triflumuron, flufenoxuron, flucycloxuron, buprofezin, pyriproxyfen, metoprene, benzoepin, diafenthiuron, imidacloprid, fipronil, nicotine sulfate, rotenone, metaldehyde, acetamiprid , Chlorfenapyr, nitenpyram, thiacloprid, clothianidin, thiamethoxam, dinotefuran, indoxacarb, pymetrozine, spinosad, emamectin, pyridalyl, tebufenozide, chromafenozide, methoxyphenozide, tolfenpyrad, machine oil, BT, insect pathogen virus, etc.

Nematicides:
Fenamifos, Phostiazate, Kazusafos etc.
Acaricide:
Chlorbenzilate, phenisobromolate, dicofol, amitraz, BPPS, benzomate, hexithiazox, fenbutazin oxide, polynactin, quinomethionate, CPCBS, tetradiphone, avermectin, milbemectin, clofentedin, cihexatin, pyridaben, fenpyroximate, tebufenpyrad, thiomidibene Dienochlor, fluacrylpyrim, acequinosyl, bifenazate, etoxazole, spirodiclofen, phenazaquin and the like.

Plant growth regulator:
Gibberellins (eg, gibberellin A3, gibberellin A4, gibberellin A7), IAA, NAA and the like.

  Next, an Example is given and this invention is demonstrated further in detail. However, the present invention is not limited to the examples.

Example 1 4- [3- (3,5-dichlorophenyl) -3-trifluoromethylpyrrolidin-1-yl] -2-methyl-N- (2-pyridylmethyl) benzoic acid amide (Compound No. 1- Production of 1) (Step 1) Production of 1-benzyl-3- (3,5-dichlorophenyl) -3-trifluoromethylpyrrolidine

  Dissolve 2.58 g of N- (trimethylsilylmethyl) -N- (n-pentyloxymethyl) benzylamine and 3.60 g of 3,5-dichloro-1- (1-trifluoromethylethenyl) benzene in 20 ml of methylene chloride. did. To this solution, 0.4 g of trifluoroacetic acid was added under ice-cooling, the mixture was returned to room temperature, and stirred at the same temperature overnight. The reaction mixture was poured into water and extracted with methylene chloride. The organic layer was washed successively with saturated aqueous sodium hydrogen carbonate and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the resulting residue was purified by silica gel column chromatography (developing solvent: ethyl acetate / n-hexane = 1/9 (volume ratio)) to obtain 2.08 g of the objective compound. Yield 63%

(Step 2) Production of 3- (3,5-dichlorophenyl) -3-trifluoromethylpyrrolidine

  1.37 g of 1-benzyl-3- (3,5-dichlorophenyl) -3-trifluoromethylpyrrolidine was dissolved in 24 ml of 1,2-dichloroethane. To this solution, 1.0 g of chloroformic acid-1-chloroethyl ester was added at room temperature, and the whole volume was heated to reflux for 5 hours. The reaction mixture was concentrated under reduced pressure, 12 ml of methanol was added, and the mixture was further heated to reflux for 2 hours. The reaction mixture was concentrated under reduced pressure, and the concentrate was poured into 5% aqueous sodium hydroxide solution and extracted with ethyl acetate. The organic layer was washed successively with water and saturated brine, and then dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the resulting residue was purified by silica gel column chromatography (developing solvent: methanol / chloroform = 1/9 (volume ratio)) to obtain 1.68 g of the target compound. Yield 93%

(Step 3) Preparation of 4- [3- (3,5-dichlorophenyl) -3-trifluoromethylpyrrolidin-1-yl] -2-methylbenzoic acid methyl ester

3- (3,5-dichlorophenyl) -3-trifluoromethylpyrrolidine (0.31 g) and 4-bromo-2-methylbenzoic acid methyl ester (0.25 g) were dissolved in toluene (6 ml), and t-butoxy sodium (0.16 g), Pd ₂ (dba) ₃ 10 mg and 2- (dicyclohexylphosphino) -2 ′-(N, N-dimethylamino) biphenyl 6 mg were added and the mixture was heated to reflux overnight under a nitrogen atmosphere. The reaction mixture was cooled, poured into water, and extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (developing solvent: ethyl acetate / n-hexane = 1/19 (volume ratio)) to obtain 0.18 g of the target compound. Yield 38%

(Step 4) Production of 4- [3- (3,5-dichlorophenyl) -3-trifluoromethylpyrrolidin-1-yl] -2-methylbenzoic acid

  0.18 g of 4- [3- (3,5-dichlorophenyl) -3-trifluoromethylpyrrolidin-1-yl] -2-methylbenzoic acid methyl ester was suspended in a mixed solvent of 10 ml of ethanol and 1 ml of water. . To this suspension, 0.17 g of potassium hydroxide was added at room temperature, and the mixture was heated to reflux for 1.5 hours. The reaction solution was concentrated under reduced pressure, poured into water, and concentrated hydrochloric acid was added to adjust to pH 1-2, followed by extraction with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate, and then the solvent was distilled off under reduced pressure to obtain 0.16 g of the objective compound. Yield 91%

(Step 5) 4- [3- (3,5-dichlorophenyl) -3-trifluoromethylpyrrolidin-1-yl] -2-methyl-N- (2-pyridylmethyl) benzoic acid amide (Compound No. 1-1) )Manufacturing of

  0.16 g of 4- [3- (3,5-dichlorophenyl) -3-trifluoromethylpyrrolidin-1-yl] -2-methylbenzoic acid was suspended in 10 ml of methylene chloride. Under ice-cooling, several drops of DMF and 0.08 g of oxalyl chloride were added to this suspension, and the mixture was returned to room temperature and stirred at the same temperature for 1.5 hours. The reaction solution is concentrated under reduced pressure to obtain a crude product of 4- [3- (3,5-dichlorophenyl) -3-trifluoromethylpyrrolidin-1-yl] -2-methylbenzoic acid chloride, which is particularly purified. It was used for the next reaction.

  0.07 g of 2-picolylamine and 0.09 g of triethylamine were dissolved in 10 ml of methylene chloride. Under ice-cooling, 4- [3- (3,5-dichlorophenyl) -3-trifluoromethylpyrrolidin-1-yl] -2-methylbenzoic acid chloride obtained above was added to this solution, and the mixture was brought to room temperature. After returning, the mixture was stirred overnight at the same temperature. The reaction solution was poured into water and extracted with chloroform. The organic layer was washed successively with water and saturated brine, and then dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the resulting residue was purified by silica gel column chromatography (developing solvent: ethyl acetate / n-hexane = 1/1 (volume ratio)) to obtain 0.13 g of the target compound. Yield 61%

The structural formula and physical constant of the compound of the present invention produced in the same manner as in Example 1 are shown in Tables 1 to 7 including the compound obtained in Example 1. The ¹ H-NMR data is shown in Table 8.

  Next, although some examples of the composition of the present invention are shown, the additive and the addition ratio are not limited to these examples, and can be varied in a wide range. Moreover, the part in a formulation Example shows a weight part.

Formulation Example 1 Wetting agent Compound of the present invention 40 parts
Clay 48 parts Dioctylsulfosuccinate sodium salt 4 parts Lignin sulfonic acid sodium salt 8 parts
The above is uniformly mixed and finely pulverized to obtain a wettable powder of 40% active ingredient.

Formulation Example 2 Emulsion Compound of the present invention 10 parts Solvesso 200 53 parts Cyclohexanone 26 parts Calcium dodecylbenzenesulfonate 1 part Polyoxyethylene alkylallyl ether 10 parts The above components are mixed and dissolved to obtain an emulsion containing 10% active ingredient.

Formulation Example 3 Powder The present compound 10 parts Clay 90 parts The above is uniformly mixed and finely pulverized to obtain a powder of 10% active ingredient.

Formulation Example 4 Granules Compound of the present invention 5 parts Clay 73 parts Bentonite 20 parts Dioctylsulfosuccinate sodium salt
1 part Potassium phosphate 1 part The above is pulverized and mixed well, water is added and kneaded well, then granulated and dried to obtain a granule of 5% active ingredient.

Formulation Example 5 Suspension Compound of the present invention 10 parts Polyoxyethylene alkyl allyl ether 4 parts Polycarboxylic acid sodium salt 2 parts Glycerin 10 parts Xanthan gum 0.2 parts Water 73.8 parts The above is mixed and the particle size is 3 microns or less The suspension is wet-pulverized until a suspension of 10% active ingredient is obtained.

Formulation Example 6 Granule wettable powder Compound of the present invention 40 parts Clay 36 parts Potassium chloride 10 parts Alkylbenzenesulfonic acid sodium salt 1 part Lignin sulfonic acid sodium salt 8 parts
Of alkylbenzenesulfonic acid sodium salt
Concentrate 5 parts or more of formaldehyde condensate uniformly and pulverize finely, add an appropriate amount of water and knead to make clay. The clay-like product is granulated and then dried to obtain a wettable powder containing 40% of the active ingredient. Examples in which the composition of the present invention obtained as described above is applied as a pest control agent are shown below.

Test Example 1 Efficacy against Cotton Aphids Adult cotton aphids were inoculated into cucumbers that had been sown for 10 days after being sown in 3-inch pots. One day later, the adult worms were removed, and a chemical solution diluted with water to a compound concentration of 125 ppm was sprayed on the cucumber infested with the larvae produced in accordance with the formulation of the emulsion shown in Formulation Example 2. It was placed in a thermostatic chamber at a temperature of 25 ° C. and a humidity of 65%, and after 5 days, the life and death were examined to determine the insecticidal rate. The test is duplicated.

As a result, the following compounds showed 100% insecticidal rate.
1-1, 1-4, 1-5, 1-6, 1-7, 1-10, 1-18, 1-19,
The insecticidal rate of Pirimi curve used as a control was 9%.

Test Example 2 Efficacy against Acacia Toyo In accordance with the formulation of the wettable powder shown in the above-mentioned Preparation Example 1, the compound was diluted with water so that the compound concentration became 125 ppm. Corn leaves were immersed in the chemical solution for 30 seconds, air-dried, placed in a petri dish with filter paper, and 5 instar larvae were inoculated. The glass lid was put on and placed in a thermostatic chamber at a temperature of 25 ° C. and a humidity of 65%. After 5 days, the survival was examined and the insecticidal rate was determined. The test is duplicated.

As a result, the following compounds showed 100% insecticidal rate.
1-1, 1-2, 1-3, 1-4, 1-5, 1-6, 1-7, 1-8, 1-9, 1-10, 1-11, 1-12, 1- 14, 1-17, 1-18, 1-19, 1-20, 1-22, 1-23, 1-24, 2-1, 3-1, 3-2, 4-2, 6-1, 7-2
The insecticide rate of chlordiform used as a control was 40%.

Test Example 3 Efficacy against mite mites On the first true leaf 7 to 10 days after germination of green beans seeded in 3 sized pots, after inoculating 17 adult females of mite mite that are resistant to organophosphate, According to the wettable powder formulation shown in Example 1, a chemical solution diluted with water was sprayed so that the compound concentration was 125 ppm. It was placed in a thermostatic chamber at a temperature of 25 ° C. and a humidity of 65%, and the rate of killing insects was examined after 3 days. The test is duplicated.

As a result, the following compounds showed 100% insecticidal rate.
1-1, 1-4, 1-10, 1-19
The insecticide rate of chlordiform used as a control was 40%.

  Conventional insecticides and acaricides have insufficient efficacy, are limited in their use due to drug resistance problems, and cause phytotoxicity and contamination of plants. There are many things that are difficult to say. Accordingly, the present invention provides a novel pesticide with low toxicity and low residence.

Claims (5)

Formula (I-2)

_Wherein, A 1, _{A 2} and _{A 3} represents a carbon atom.
X represents a methylene group.
Y represents a halogen atom or a C1-C6 alkyl group.
n represents an integer of 0 to 4. When n is 2 or more, the plurality of Y may be the same as or different from each other.
Q represents a halogen atom, a cyano group, Cl -C 12 haloalkyl group, a hydroxyl group, C1 -C6 alkoxy, or a group represented by _-CO 2 _{R 8.}
R ₈ represents a C1-C12 alkyl group.
Z represents an unsubstituted or substituted phenyl group.
R ₁ and R ₂ each independently represent a hydrogen atom, a C1-C12 alkyl group optionally substituted by G , or a group represented by —N (R ₁₃ ) (R ₁₄ ).
R ₁₃ and R ₁₄ each independently represents a hydrogen atom or an unsubstituted or substituted heterocyclic group.
G represents a group represented by —OR ₁₆ , an unsubstituted or substituted phenyl group, or an unsubstituted or substituted heterocyclic group.
R ₁₆ represents a C1-C12 alkyl group. ]
Or a salt thereof. In the formula (I-2), Z represents the following formula (Z-1)

(In the formula, r represents a halogen atom, and m0 represents an integer of 0 to 5.)
The nitrogen-containing heterocyclic compound or a salt thereof according to claim 1, wherein the nitrogen-containing heterocyclic compound is a group represented by the formula: A pest control agent comprising at least one of the nitrogen-containing heterocyclic compound or a salt thereof according to claim 1 or 2 as an active ingredient. The pest control agent according to claim 3 , which is an insecticide. The pest control agent according to claim 3 , which is an acaricide.